diff --git a/enterprise/app/models/captain/assistant.rb b/enterprise/app/models/captain/assistant.rb
index ac5876bef..ea67b42cd 100644
--- a/enterprise/app/models/captain/assistant.rb
+++ b/enterprise/app/models/captain/assistant.rb
@@ -77,7 +77,10 @@ class Captain::Assistant < ApplicationRecord
   end
 
   def agent_tools
-    [self.class.resolve_tool_class('faq_lookup').new(self)]
+    [
+      self.class.resolve_tool_class('faq_lookup').new(self),
+      self.class.resolve_tool_class('handoff').new(self)
+    ]
   end
 
   def prompt_context
diff --git a/enterprise/lib/captain/prompts/assistant.liquid b/enterprise/lib/captain/prompts/assistant.liquid
index 2c1f50155..21bcc8d94 100644
--- a/enterprise/lib/captain/prompts/assistant.liquid
+++ b/enterprise/lib/captain/prompts/assistant.liquid
@@ -53,8 +53,12 @@ You can use markdown to format your response
   "reasoning": "Used search_contact tool to locate the contact by email address"
 }
 
-# Special Cases
-When the user explicitly requests to speak with a human agent, return:
-{"response": "conversation_handoff", "reasoning": "User requested human agent assistance"}
+# Human Handoff
+When the user explicitly requests to speak with a human agent, or when you cannot adequately assist them, use the handoff tool to transfer the conversation to a human support agent. Provide a clear reason for the handoff when using the tool.
+
+Examples:
+- User asks to speak with human: Use handoff tool with reason "User requested human agent assistance"
+- Cannot find answer in FAQ: Use handoff tool with reason "Unable to find relevant information in knowledge base"
+- Complex issue beyond capabilities: Use handoff tool with reason "Issue requires specialized human expertise"
 
 Remember: Never mention handoffs or agent transfers to the user. Handle them seamlessly.